Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago O'Hare Intl Airport to Caribbean from $57

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago O'Hare Intl Airport to Caribbean departing on 12/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Deals available from 900+ travel sites.

"This year, momondo is the #1 place for airfares on the internet."
Save money when you book flights with momondo
Big names and deals
Big names and deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customize your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? to track prices.

Find the cheapest flights from Chicago O'Hare Intl Airport to Caribbean

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago O'Hare Intl Airport to Caribbean that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago O'Hare Intl Airport to Caribbean.

Cheap last minute flights

Planning a quick getaway from Chicago O'Hare Intl Airport to Caribbean? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Caribbean, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago O'Hare Intl Airport to Caribbean

Find recent round-trip train or bus tickets from Chicago O'Hare Intl Airport to Caribbean.

All round-trip flight deals to Caribbean

The cheapest plane tickets to Caribbean found on KAYAK recently.
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$117Spirit Airlines
Find Deal
Tue, Jan 21 - Wed, Jan 29
4:58 pm - 2:02 amORD-SJU
7h 04m1 stop
10:01 pm - 9:24 amSJU-ORD
13h 23m1 stop
$128Frontier
Find Deal
Mon, Dec 9 - Tue, Dec 17
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
2:05 am - 9:43 amSJU-ORD
9h 38m1 stop
$226United Airlines
Find Deal
Mon, Dec 9 - Fri, Dec 13
12:53 pm - 12:36 amORD-SJU
9h 43m1 stop
2:05 am - 10:53 amSJU-ORD
10h 48m1 stop
$255United Airlines
Find Deal
Mon, Dec 9 - Fri, Dec 13
5:10 am - 3:49 pmORD-PUJ
8h 39m2 stops
5:05 pm - 12:09 amPUJ-ORD
9h 04m1 stop
$345American Airlines
Find Deal
Tue, Jan 7 - Tue, Jan 14
8:25 pm - 11:55 amORD-PUJ
13h 30m1 stop
5:05 pm - 12:09 amPUJ-ORD
9h 04m1 stop
$353American Airlines
Find Deal
Sat, Jan 11 - Wed, Jan 15
6:15 am - 5:15 pmORD-PUJ
9h 00m1 stop
2:02 pm - 8:48 pmPUJ-ORD
8h 46m1 stop
$363Delta
Find Deal
Fri, Jan 10 - Fri, Jan 17
7:05 am - 3:24 pmORD-MBJ
7h 19m1 stop
4:49 pm - 11:59 pmMBJ-ORD
8h 10m1 stop
$469Delta
Find Deal
Tue, Feb 18 - Wed, Feb 26
7:19 am - 1:40 pmORD-GCM
29h 21m1 stop
4:00 pm - 7:32 pmGCM-ORD
28h 32m1 stop
$617Air Canada
Find Deal
Thu, Dec 5 - Sun, Dec 8
3:35 pm - 1:40 pmORD-GCM
21h 05m2 stops
2:40 pm - 10:54 amGCM-ORD
21h 14m2 stops
$621Air Canada
Find Deal
Thu, Feb 20 - Thu, Feb 27
4:58 pm - 2:02 amORD-SJU
7h 04m1 stop
$57Frontier
Find Deal
Mon, Dec 9
9:32 am - 4:15 pmORD-SJU
4h 43mnonstop
$58Spirit Airlines
Find Deal
Wed, Jan 1
1:15 pm - 10:22 pmORD-SJU
7h 07m1 stop
$105United Airlines
Find Deal
Sat, Jan 25
5:45 am - 3:25 pmORD-PUJ
7h 40m1 stop
$165Delta
Find Deal
Tue, Jan 14
10:43 am - 5:11 pmORD-PUJ
4h 28mnonstop
$171United Airlines
Find Deal
Fri, Jan 24
6:15 am - 5:15 pmORD-PUJ
9h 00m1 stop
$175Delta
Find Deal
Fri, Feb 28
5:30 pm - 11:40 amORD-PUJ
16h 10m1 stop
$185American Airlines
Find Deal
Sat, Dec 7
7:09 pm - 12:34 pmORD-PUJ
15h 25m1 stop
$209American Airlines
Find Deal
Sat, Mar 1
7:25 pm - 11:02 amORD-PLS
14h 37m1 stop
$250JetBlue
Find Deal
Tue, May 20
7:25 pm - 11:02 amORD-PLS
14h 37m1 stop
$263JetBlue
Find Deal
Sat, May 17
1:09 pm - 11:40 pmORD-SJU
8h 31m1 stop
12:57 pm - 12:33 amSJU-ORD
13h 36m1 stop
$237Spirit Airlines
Find Deal
Sun, Nov 24 - Fri, Dec 6
1:09 pm - 11:40 pmORD-SJU
8h 31m1 stop
2:17 pm - 5:47 pmSJU-ORD
5h 30mnonstop
$250Spirit Airlines
Find Deal
Sun, Nov 24 - Thu, Dec 5
2:46 pm - 12:33 amORD-SJU
7h 47m1 stop
9:49 pm - 9:54 amSJU-ORD
14h 05m1 stop
$258Frontier
Find Deal
Tue, Nov 26 - Thu, Dec 5
8:21 pm - 10:57 amORD-SJU
12h 36m1 stop
9:49 pm - 9:54 amSJU-ORD
14h 05m1 stop
$264Frontier
Find Deal
Sun, Nov 24 - Thu, Dec 5
7:05 am - 5:10 pmORD-SJU
8h 05m1 stop
7:10 am - 5:15 pmSJU-ORD
12h 05m1 stop
$369Delta
Find Deal
Mon, Nov 25 - Fri, Dec 6
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
5:50 pm - 11:20 pmSJU-ORD
7h 30m1 stop
$398United Airlines
Find Deal
Tue, Nov 26 - Wed, Dec 4
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
4:52 pm - 8:11 pmSJU-ORD
5h 19mnonstop
$405United Airlines
Find Deal
Sun, Nov 24 - Mon, Nov 25
6:00 am - 2:31 pmORD-SJU
6h 31m1 stop
3:41 pm - 11:59 pmSJU-ORD
10h 18m1 stop
$414Delta
Find Deal
Sun, Nov 24 - Mon, Nov 25
8:12 am - 2:37 pmORD-PUJ
4h 25mnonstop
4:55 pm - 8:45 amPUJ-ORD
17h 50m1 stop
$454American Airlines
Find Deal
Mon, Nov 25 - Sat, Dec 7
4:29 pm - 11:45 amORD-PUJ
17h 16m1 stop
4:55 pm - 8:45 amPUJ-ORD
17h 50m1 stop
$458American Airlines
Find Deal
Mon, Nov 25 - Sat, Dec 7
1:00 pm - 7:36 pmORD-SJU
4h 36mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$158Spirit Airlines
Find Deal
Tue, Jan 7 - Tue, Jan 14
1:44 pm - 8:21 pmORD-SJU
4h 37mnonstop
9:26 pm - 12:51 amSJU-ORD
5h 25mnonstop
$159Spirit Airlines
Find Deal
Fri, Jan 24 - Wed, Jan 29
6:00 am - 12:29 pmORD-PUJ
4h 29mnonstop
6:45 pm - 9:59 pmPUJ-ORD
5h 14mnonstop
$190Frontier
Find Deal
Tue, Jan 7 - Tue, Jan 14
6:00 am - 12:29 pmORD-PUJ
4h 29mnonstop
6:45 pm - 9:59 pmPUJ-ORD
5h 14mnonstop
$193Frontier
Find Deal
Tue, Jan 7 - Tue, Jan 14
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
4:52 pm - 8:11 pmSJU-ORD
5h 19mnonstop
$321United Airlines
Find Deal
Fri, Feb 28 - Thu, Mar 6
8:05 am - 2:40 pmORD-SJU
4h 35mnonstop
3:36 pm - 7:06 pmSJU-ORD
5h 30mnonstop
$354American Airlines
Find Deal
Wed, Dec 11 - Tue, Dec 17
8:05 am - 1:45 pmORD-SJU
4h 40mnonstop
3:25 pm - 7:40 pmSJU-ORD
5h 15mnonstop
$375American Airlines
Find Deal
Wed, May 14 - Thu, May 29
2:20 pm - 8:55 pmORD-SJU
4h 35mnonstop
8:35 am - 11:54 amSJU-ORD
5h 19mnonstop
$389United Airlines
Find Deal
Sat, Dec 7 - Wed, Dec 11
8:45 am - 1:52 pmORD-PLS
4h 07mnonstop
2:30 pm - 6:08 pmPLS-ORD
4h 38mnonstop
$713Lufthansa
Find Deal
Fri, Dec 20 - Fri, Dec 27
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$729Lufthansa
Find Deal
Sun, Jan 5 - Sun, Jan 12

Frontier flights from Chicago O'Hare Intl Airport to Caribbean

Our best Frontier deals on Chicago O'Hare Intl Airport to Caribbean flight tickets
Frontier
Dec 9
ORD4:58 pmChicago O'Hare Intl
7h 04m
1 stop
SJU2:02 amSan Juan Luis Munoz Marin Intl
Dec 17
SJU10:01 pmSan Juan Luis Munoz Marin Intl
13h 23m
1 stop
ORD9:24 amChicago O'Hare Intl
Frontier
Feb 22
ORD8:44 pmChicago O'Hare Intl
10h 51m
1 stop
SJU9:35 amSan Juan Luis Munoz Marin Intl
Feb 26
SJU6:35 amSan Juan Luis Munoz Marin Intl
9h 50m
1 stop
ORD2:25 pmChicago O'Hare Intl
Frontier
Dec 6
ORD6:07 pmChicago O'Hare Intl
21h 16m
1 stop
SJU5:23 pmSan Juan Luis Munoz Marin Intl
Dec 12
SJU7:16 pmSan Juan Luis Munoz Marin Intl
16h 38m
1 stop
ORD9:54 amChicago O'Hare Intl

Spirit Airlines flights from Chicago O'Hare Intl Airport to Caribbean

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to Caribbean flight tickets
Spirit Airlines
Jan 21
ORD1:44 pmChicago O'Hare Intl
4h 37m
SJU8:21 pmSan Juan Luis Munoz Marin Intl
Jan 29
SJU9:26 pmSan Juan Luis Munoz Marin Intl
5h 25m
ORD12:51 amChicago O'Hare Intl
Spirit Airlines
Jan 6
ORD1:00 pmChicago O'Hare Intl
4h 36m
SJU7:36 pmSan Juan Luis Munoz Marin Intl
Jan 15
SJU9:26 pmSan Juan Luis Munoz Marin Intl
5h 25m
ORD12:51 amChicago O'Hare Intl
Spirit Airlines
Jan 6
ORD1:00 pmChicago O'Hare Intl
4h 36m
SJU7:36 pmSan Juan Luis Munoz Marin Intl
Jan 15
SJU9:26 pmSan Juan Luis Munoz Marin Intl
5h 25m
ORD12:51 amChicago O'Hare Intl

See travel insights to Caribbean from

How to get the cheapest flight ticket from Chicago O'Hare Intl Airport to Caribbean

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Caribbean?

The cheapest day to depart from Chicago O'Hare Intl Airport to Caribbean is on a Tuesday when prices can be found for as low as $355. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $415. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean.

What is the cheapest Chicago O'Hare Intl to Caribbean flight route?

Fly from Chicago O'Hare Intl to San Juan Luis Munoz Marin Intl for the best Chicago O'Hare Intl - Caribbean flight prices

What cabin class options are available on Chicago O'Hare Intl to Caribbean flights?

There are 4 cabin classes available to choose from on Chicago O'Hare Intl to Caribbean flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago O'Hare Intl Airport to Caribbean flights?

You could potentially save up to 1% on your flight if you consider stops on a Chicago O'Hare Intl Airport to Caribbean flight.

Cheap Chicago O'Hare Intl Airport to Caribbean flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Caribbean

Best Price Found

$57

Fastest flight time

3h 21m

Direct flights

Every day

Airports in Caribbean

6 airports
The best one-way flight to Caribbean from Chicago O'Hare Intl Airport in the past 72 hours is $57. The best round-trip flight deal from Chicago O'Hare Intl Airport to Caribbean found on momondo in the last 72 hours is $117.
The fastest flight from Chicago O'Hare Intl Airport to Caribbean takes 3h 21m
Direct flights go from Chicago O'Hare Intl Airport to Caribbean every day.
There are 6 airports near Caribbean: George Town Owen Roberts Intl (GCM), Nassau Intl (NAS), Punta Cana (PUJ), Montego Bay Sangster Intl (MBJ), Providenciales (PLS), San Juan Luis Munoz Marin Intl (SJU)

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Caribbean?

    Prices for flights from Chicago O'Hare Intl Airport to Caribbean refresh daily.

  • How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Caribbean?

  • How old do you have to be to fly from Chicago O'Hare Intl Airport to Caribbean?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport to Caribbean.

  • What documentation or ID do you need to fly to Caribbean?

    The travel and health documents required for your trip to Caribbean can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Chicago O'Hare Intl Airport to Caribbean?


Best airlines flying from Chicago O'Hare Intl Airport to Caribbean

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Caribbean with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $65Free CancellationRating
6.1
3,536 reviews
Search Frontier flights
JetBluePriceFrom $137Free CancellationRating
7.4
3,389 reviews
Search JetBlue flights
Spirit AirlinesPriceFrom $166Free CancellationRating
6.3
8,169 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $267Free CancellationRating
7.4
9,172 reviews
Search United Airlines flights
DeltaPriceFrom $324Free CancellationRating
8.0
8,755 reviews
Search Delta flights
American AirlinesPriceFrom $324Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $379Free CancellationRating
8.1
5,005 reviews
Search Southwest flights
Copa AirlinesPriceFrom $379Free CancellationRating
7.7
1,779 reviews
Search Copa Airlines flights
Air CanadaPriceFrom $514Free CancellationRating
7.0
8,246 reviews
Search Air Canada flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Caribbean?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Caribbean for you.

Can I find flights from Chicago to Caribbean with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Caribbean from Chicago with this policy.

How can momondo help me find flights from Chicago to Caribbean?

Once all potential Chicago to Caribbean flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Chicago to Caribbean right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Caribbean, momondo offers a useful price alert feature which will track prices for flights to Caribbean from Chicago and alert you when they change.


An easier way to manage your Caribbean trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Tue 11/26
Tue 12/3
Email me momondo's favorite deals

Find better results for your trip to Caribbean

Popular cities in Caribbean

Popular flights according to clicks in the last 7 days on momondo